(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

• ChemBase ID: 119519
• Molecular Formular: C41H76N2O15
• Molecular Mass: 837.04654
• Monoisotopic Mass: 836.52456974
• SMILES: [C@@H]1([C@@H]([C@H](C[C@H](O1)C)N(C)C)O)O[C@@H]1[C@H]([C@@H]([C@H](C(=O)O[C@@H]([C@]([C@@H]([C@H](/C(=N/OCOCCOC)/[C@@H](C[C@]1(O)C)C)C)O)(O)C)CC)C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C
• Canonical SMILES: COCCOCO/N=C/1\[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
• InChIKey: RXZBMPWDPOLZGW-XMRMVWPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• IUPAC Traditional name: (E)-roxithromycin; (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• Synonyms: (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltet rahydro-2H-pyran-2-yl)oxy)-10-(((2-methoxyethoxy)methox y)imino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one; Abbotic; Antibiotic RU 28965; Azuril; Cirumycin; Macrosil; Roxitrol; Rulide; Roxithromycin; (9E)-9-[O-[(2-Methoxyethoxy)methyl]oxime] Erythromycin; Assoral; Brilid; Claramid; Forilin; Overal; RU 28965; RU 965; Rossitrol; Rotramin; Roxeptin; Roxid; Roxithromycin; Roxithromycin A; Rulid; Surlid; Roxithromycin

Database IDs

• CAS Number: 80214-83-1
• PubChem SID: 162107641
• PubChem CID: 6915744

CALCULATED PROPERTIES

• Acid pKa: 12.454023
• H Acceptors: 16
• H Donor: 5
• LogD (pH = 5.5): -0.23886713
• LogD (pH = 7.4): 1.3162447
• Log P: 2.9999793
• Molar Refractivity: 211.2376 cm^3
• Polarizability: 85.90249 Å^3
• Polar Surface Area: 216.89 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 111-118°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Binds to the 50S subunit of ribosome; Protein synthesis inhibitor

Product Information

• Application(s): Antibiotic; Immunomodulator; Shows a similar range of antibacterial activity to Erythromycin BDQ81-E but is much more active in vivo

DETAILS

Toronto Research Chemicals - R700850

Semisynthetic Erythromycin derivative. Antibacterial.

REFERENCES

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